2-烯丙基-3-甲氧基-环己-2-烯-1-酮 | 85696-84-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 2-烯丙基-3-甲氧基-环己-2-烯-1-酮
• 英文名称: 3-methoxy-2-(propen-2-yl)cyclohex-2-en-1-one
• 英文别名: 3-Methoxy-2-(2-propenyl)-2-cyclohexenone；2-allyl-3-methoxy-2-cyclohexenone；2-allyl-3-methoxycyclohex-2-en-1-one；2-Cyclohexen-1-one, 3-methoxy-2-(2-propenyl)-；3-methoxy-2-prop-2-enylcyclohex-2-en-1-one
• CAS: 85696-84-0
• 化学式: C₁₀H₁₄O₂
• mdl: MFCD18813725
• 分子量: 166.22
• InChiKey: QUFVSAZDPAWYBF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2914509090

反应信息

• 作为反应物：
  描述：

  2-烯丙基-3-甲氧基-环己-2-烯-1-酮 在 二异丁基氢化铝 作用下， 以 乙醚 、 甲苯 为溶剂， 生成 2-(丙-2-烯基)环己-2-烯-1-酮
  参考文献：
  名称：

  An Efficient Method for Construction of the Angularly Fused 6,3,5-Tricyclic Skeleton of Mycorrhizin A and Its Analogues

  摘要：

  The angularly fused 6,3,5-tricyclic system is readily generated via a cascade cyclization under acid promotion. The reaction proceeds at room temperature with high stereochemical fidelity from the electrophilic center of the epoxide to the cyclopropane product. This methodology provides a potentially useful approach for the synthesis of mycorrhizin A and its analogues.

  DOI：

  10.1021/ol8026895
• 作为产物：
  描述：

  1,3-环己二酮 在 铜 、 potassium carbonate 、 potassium hydroxide 作用下， 以 水 、 丙酮 为溶剂， 反应 6.0h， 生成 2-烯丙基-3-甲氧基-环己-2-烯-1-酮
  参考文献：
  名称：

  From Chiral ortho-Benzoquinone Monoketals to Nonracemic Indolinocodeines through Diels–Alder and Cope Reactions

  摘要：

  The S-dienol (-)-4 containing 10 carbons and one oxygen of the final product was prepared in 98.6% ee and 39% yield from cyclohexan-1,3-dione. It was attached to the aromatic ring as a monoether of catechol S-(-)-6 and subsequently subjected to oxidative ketalization in methanol. The allylated phenanthrofuran obtained was selectively oxidized at the terminal double bond. The fifth ring was completed by a "one-pot" amidation cyclization process promoted by palladium acetate. The final homochiral indolinocodeine (-)-31 was obtained in 16 steps and 3.6% overall yield from cyclohexan-1,3-dione.

  DOI：

  10.1021/jo3014098

文献信息

• Total Synthesis of (+)-Lyconadin A and Related Compounds via Oxidative C−N Bond Formation
  作者：Scott P. West、Alakesh Bisai、Andrew D. Lim、Raja R. Narayan、Richmond Sarpong

  DOI：10.1021/ja903868n

  日期：2009.8.12

  fundamental bond construction in organic synthesis and is indispensable for the synthesis of alkaloid natural products. In the context of the synthesis of the architecturally complex Lycopodium alkaloid lyconadin A, we have discovered a highly efficient oxidative C-N bond forming reaction that relies on the union of a nitrogen anion and a carbon anion. Empirical evidence amassed during our synthetic studies

  碳氮（CN）键的形成是有机合成中的基本键结构，是合成生物碱天然产物必不可少的。在合成结构复杂的石松生物碱 lyconadin A 的背景下，我们发现了一种高效的氧化 CN 键形成反应，该反应依赖于氮阴离子和碳阴离子的结合。在我们的合成研究中积累的经验证据表明，CN 键形成过程的机制包括极性过程和自由基过程。在此，我们介绍了我们对这种新型 CN 键形成反应的研究及其在 lyconadin A 和相关衍生物的对映选择性全合成中的应用。
• Developing the Saegusa–Ito Cyclisation for the Synthesis of Difluorinated Cyclohexenones
  作者：Jonathan M. Percy、Adam W. McCarter、Alan L. Sewell、Nikki Sloan、Alan R. Kennedy、David J. Hirst

  DOI：10.1002/chem.201503653

  日期：2015.12.21

  the turnover of the initial palladium(II) salt, whereas the provision of an oxygen atmosphere ensured more rapid reaction. Annulations required a minimum level of substitution on the chain, but failed when the alkene was substituted. Annelations allowed a range of n,6‐bicyclic systems to be prepared and afforded three products, in which heterocycles were fused to the new cyclohexenone. The least substituted

  钯（II）催化的环烯基化反应（Saegusa–Ito环化）首次用于在温和条件下将二氟甲硅烷基醚转化为二氟环烯酮。甲硅烷基醚前体是从三氟乙醇分两个高产步骤制备的，并以中等至良好的收率环化。空气和氯化铜（I）在乙腈中的混合产生了初始钯（II）盐的周转，而提供氧气气氛则确保了更快速的反应。必须在链上进行最低限度的取代，但是当烯烃被取代时，失败了。退火允许制备一系列n，6-双环系统，并提供三种产物，其中杂环与新的环己烯酮稠合。
• Toward the Total Synthesis of Palhinine A: Expedient Assembly of Multifunctionalized Isotwistane Ring System with Contiguous Quaternary Stereocenters
  作者：Guo-Biao Zhang、Fang-Xin Wang、Ji-Yuan Du、Hu Qu、Xiao-Yan Ma、Meng-Xue Wei、Cheng-Tao Wang、Qiong Li、Chun-An Fan

  DOI：10.1021/ol301534r

  日期：2012.7.20

  The stereoselective, expedient assembly of the key functionalized isotwistane (bridged tricyclo[4.3.1.03,7]decane) system, 5/6/6 ring, with contiguous quaternary stereocenters in Lycopodium alkaloid palhinine A and its analogues via an intramolecular Diels–Alder strategy is described.

  立体选择性，有利的关键官能isotwistane的组件（桥接三环[4.3.1.0 3,7 ]癸烷）系统，5/6/6环，具有连续的季立体在石松生物碱palhinine A及其类似物通过分子内狄尔斯-阿尔德策略进行了描述。
• Unified Strategy for the Synthesis of the “Miscellaneous” <i>Lycopodium</i> Alkaloids: Total Synthesis of (±)-Lyconadin A
  作者：Alakesh Bisai、Scott P. West、Richmond Sarpong

  DOI：10.1021/ja8028069

  日期：2008.6.1

  Total synthesis of the Lycopodium alkaloid lyconadin A was achieved in 18 steps starting from a readily available vinylogous ester and bromopicoline. The key step in the total synthesis is a proximity-driven oxidative C-N bond-forming reaction that yields the lyconadin pentacycle from a tetracyclic precursor. The key tetracycle, which has been prepared for the first time, is a versatile intermediate

  石松生物碱 lyconadin A 的全合成是从容易获得的乙烯酯和溴甲基吡啶开始的 18 个步骤中实现的。全合成的关键步骤是邻近驱动的氧化 CN 键形成反应，该反应从四环前体产生lyconadin 五环。首次制备的关键四环是一种多功能中间体，可用于多种石松生物碱的全合成。该计划成功的关键是有效制备吡啶环化的环庚二烯三环，它有望成为获取各种含有天然产物的七元环的通用策略。
• Isomerisation of ω-alkenyl substituted cyclohexane-1,3-dione enol derivatives using rhodium catalysis. A practical synthesis of substituted resorcinols
  作者：Ian S. Blagbrough、Gerald Pattenden、Richard A. Raphael

  DOI：10.1016/s0040-4039(00)85728-7

  日期：1982.1

  Treatment of the ω-alkenyl substituted cyclohexane-1,3-dione enol derivatives (1), (11), and (13) with rhodium trichloride trihydrate leads to the corresponding resorcinol derivatives (2), (12), and (15) respectively. By contrast, the RhCl3.3H2O catalysed isomerisations of the related enol ethers (5) and (9) instead produce the dienones (6) and (10) respectively.

  用三水合三水合铑处理ω-烯基取代的环己烷-1,3-二酮烯醇衍生物（1），（11）和（13）得到相应的间苯二酚衍生物（2），（12）和（15）分别。相反，相关的烯醇醚（5）和（9）的RhCl 3 .3H 2 O催化的异构化分别产生二烯酮（6）和（10）。